Trial and Error
by Kuroda Masquerade
Summary: When Toothless and his rider become separated and stranded on a desolate island, their experiences will become very different as they not only struggle to find each other and escape, but live through their ordeals when Toothless falls into the hands of an unknown viking tribe and Hiccup fights to survive his own obstacles. Rated T currently, but will change.


**a/n: Hello! nny94 here (co-writer). This story came to be while chatting with Kuro and we decided we wanted to put something dark out there into the HTTYD fanfictions. We'll try to be updating this story when we can and Kuro and I will be working the entire way to the end together. Hope you like this first chapter and get tied into keep reading this story.**

**a/n: POVs may vary per chapter, but will eventually settle to one. The content that may appear in this story is not for the weak of heart, viewer discretion is advised. Nevertheless, hope you all enjoy it. Credit to Nathan Fowkes for the image (I made some edits though) -Kuro (main-writer)**

The rocky cliff sides of Outcast Island were momentarily lit by a flash of lightning as rain poured over the land, followed by a deafening clap of thunder. It was mid-summer and the warm temperatures attracted many storms. The rains would be welcomed with open arms in all other places where lush, green life grew, but not such existed here. The waters only continued to feed into the despair. Down in the prison underground were many dragons, forever they lived in their stony dark prison of steel bars, skimpy rations and neglect. This was one of the few hells that existed in the world today, a place where fear grew among the winged monsters. A place where they knew they would die, knowing that escape from here was impossible, but their minds would refuse and fight, escape, or die trying. Though for some of these fire breathing reptiles, the neglect of these Vikings was a blessing compared to the attention that some received.

In the arena, the crack of a whip could be heard as a young and small mossy colored Deadly Nadder cowered in a corner, confronted by a Viking clad in armor and sporting a bushy black beard and a helmet topped with horns as twisted as the Viking himself. His rotted yellow teeth bore in anger at the beast as he went to crack the whip against the dragon's scales for the umpteenth time. He held a shield in his other hand that warded off any attacks, but whether it _would_ attack was questionable; for Alvin was a treacherous Viking with a fearsome reputation. All of the dragons who lived here knew better than to misbehave in his presence. Though some were still learning their lesson; as the Nadder let out a shriek and charged him, Alvin drew back and slammed his fist into the beasts jaw. The trapped Nadder recoiled and ran to the side before releasing a bellow of sparking hot flame right towards the Viking. Alvin dodged the fire, and removed his long crooked sword and hurled it at the dragon. The weapon spun twice in the air before lodging itself deep into the green scales. The Nadder sank to the ground, and Alvin approached it. Reaching down and pulling the sword out of the shuddering dragon. He sheathed his sword, not caring of the blood that has not been cleaned from it yet.

"Alvin!" He heard his name called from the entrance to the ring, and he turned. He was frustrated at another failed attempt to tame a dragon. No matter how hard he tried to gain a dragon's trust, he could never reach it, and no matter how hard he tried to capture his doorway into that world; Hiccup, something always got in the way. However he knew it would only be a matter of time until he could get his hands on the scrawny Hooligan once more.

"What now?" He responded impatiently, glaring at the Viking. The vile man was in no mood to be disturbed after another failed attempt added to his countless shortcomings. "The Rugged Raiders' chief is here." The man spoke to Alvin informing him with a dip of his head, before turning and running back up the path to go to the dock. Alvin grumbled and looked back at the Nadder, now lifeless; before he followed the other Viking. Taking another one of the scaled beasts' life hadn't of phased the crude man one bit, the only thing he cared to do with the dragons was to get them to serve under his boot. The rain let up greatly when Alvin reached the dock, and he stood with a coarse stance. The men on the ship are skinny, but even Alvin can see the brute muscle under their clothing. These Vikings held a rough look to them, as if they'd been to Neiflheim and back but still kept their wits about them. Alvin watched as a dozen men got off the ship, all lining up to await the step off of their chieftain respectfully. Alvin was thinking to himself why his men didn't do that. He thought this with selfishness he couldn't see, but kept his mouth closed for now. Soon after the men got off came the chief, who's trimmed blonde hair reached to his ears and his triangular face was lined with a thick but short beard and topped with a silver horned helmet. He scanned the Outcasts with observant green eyes. He had a calm look to him, like he knew exactly what he was doing while approaching the larger Outcast leader with confident long strides. A dark colored cloak hanging loosely behind his lightly armored body. This cloak was sleek as it was ragged; it was fit for a ruler, but also gave the appearance of a warrior.

"Alvin…" He greeted in a calm and deep voice. He was just as tall as Alvin, but not as buff. Alvin eyed him skeptically. "Took ye' long enough te' get here..." He complained, flashing a toothy scowl. "…Baldor."

Baldor The Bad didn't have half the reputation that Alvin had. His tribe was known for their hostility but they did not blindly go around and start trouble like the Outcasts did. Baldor was smart about his attacks; his whole tribe was smarter than the most. Their island was unknown to all and virtually didn't exist on any maps. Broken Rock Island was all but uninhabitable and lifeless as Hel's doorstep. No one thinks that a tribe of Vikings may live there on the salty sea beaten island of jagged cliffs and wrecks. Nothing lives there; nothing could, so it passes through the radar of all who know of it. The Rugged Raiders however have adapted to the harshness of their island that they've come to love. They are skinny because no food grows there, but they are tough because they've learned to survive. As a tribe that values its gold more than its food supplies, Baldor sends many ships on nearby villages to pillage and raid; only to disappear back to the sea, never followed, never sought out because those who know of them can never discover their hideout. But that's not the only edge they hold, and Alvin knows it.

"I apologize… the seas are unpredictable." Baldor responded with a lowered head for respect.

Alvin huffed, and eyed him suspiciously before he turned. "Come on then… we got lots to discuss." Baldor raised his hand towards his men, gesturing for two to follow and the rest to remain. Two of the men nodded their heads at each other and followed obediently, traveling the hard path right behind their revered leader. Alvin led the three into a winding cave structure, lit by flickering orange torches. The dank stench of mold riddled this place; it held both a disgusting and intimidating factor to it. Not that mold is direly terrifying, but for the reason that Alvin lived here and thrived here. Not just anyone could do such a thing, but a man and men of many lows.

Eventually they came to a room; in the middle was a table with some parchment atop it, and in the corner slept a Terrible Terror chained to the wall on a straw mat. The small dragon opened his eyes and raised his head upon their entrance. He quickly sat up to be on his guard. Alvin ignored the Terror and went to the table. He seemed to be in thought, as if choosing his first words carefully; something he rarely did.

Baldor wasted no time to start the discussion.

Across the sea, there was no rain and the sky was blue as a Nadder's pristine hide. Hiccup walked out of his home on Berk, followed closely by his black scaled friend. The sun's rays of light lit up the land around, exposing the true beauty that belonged to the island of Berk, though rarely noticed by the brutes that lived here. It had been about a week since Alvins' last failed attempt to capture Hiccup. The village was on edge, as the Outcasts seemed to be hatching better plans each time. Stoic in particular showed concern. Hiccup knew what was on the chief's mind as he stayed up late at night, stoking the fire with his eyes fixed on something the boy could not see. But Hiccup actually felt a bit of confidence towards the quarrel he had with Alvin, something that was unknown to the scrawny Horrendous Haddock. He knew that Alvin wanted him and the Book of Dragons, but his last attempt to capture Hiccup had failed miserably. No matter what Alvin had planned, the Hairy Hooligans were always one step ahead thanks to the boy who ended the great dragon war. Hiccup knew that as long as he had Toothless by his side, he would be able to outsmart the Outcast who has caused so much trouble. However he knew not to be too confident and he was always on his guard when away from home.

Those thoughts were not on his mind now though, as he prepared for a flight with his friend before breakfast. "You ready?" He asked Toothless, who responded with a happy grumble as the Viking climbed onto his back. Hiccup locked his prosthetic into place and wiggled it to make sure it was secured, and after a glance behind him to make sure all was well with the bright red tailfin, he turned back and grinned. "Let's go!" And with that, Toothless opened his wings and let his tongue hang from his mouth as he left the ground behind.

Hiccup's father awoke soon after his son and Toothless were gone. The man was like a bear awaking from a deep slumber, something with even half a brain would never mess with. He looked up the stairs and called out, "Hiccup!" Unsure of he's even still in the house. "Toothless," he also called out and met no response from the two members of his family. _They must be out flying already,_ he thought to himself putting a large grin on his face. Even though there were troubles, one could not ignore the better times that existed for his village and his loved ones. He went back and to the fire pit and lit the flames to get it started again. _Alvin, you'll never be a match for me or my son, we both know that._ He played with the fire a bit, poking at it like he did last night, but soon knew he would have to go out and run his village again. Keeping everything in check, making sure nothing is wrong.

The Night Fury ascended high above the village and eventually soared over Raven Point, Hiccup rode comfortably on his back as he gazed at the jagged snowcap below. The trees on the mountain held their dark green leaves proudly; the ecosystem was very much alive on their small island. Hiccup gripped his saddle tightly as Toothless started climbing higher into the sky. This was the only place the boy felt truly at peace, flying on his best friend. The two had been through everything together, always there to keep the other going through the hard and good times. Away from the hectic life of the village and Training Arena, he could listen to the wind in his ears and smell the fresh air while Toothless stretched his wings happily. The night fury had given his life to the boy as Hiccup had done for him; the two were always to be inseparable.

Toothless banked left after a few minutes, and flew towards the sea.


End file.
